반응 #51886

반응 방정식

3,4,5-trifluorobenzonitrile

diethanolamine

→

3,5-difluoro-4-[bis(2-hydroxyethyl)amino]benzonitrile

용매

N,N-dimethylacetamide

반응 조건

후처리

1. 1
   기타The solvent was then evaporated
2. 2
   기타the residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml)
3. 3
   건조the organic layer dried (MgSO4)
4. 4
   기타evaporated to dryness
5. 5
   기타The residue was chromatographed
6. 6
   기타to give
7. 7
   기타after recrystallization from toluene, 2.7 g (35%) of pure white crystals

실험 절차

A solution of 3,4,5-trifluorobenzonitrile (5 g, 32 mmol) and diethanolamine (6 ml, 85 mmol) in N,N-dimethylacetamide was stirred for 10 days. The solvent was then evaporated, the residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml), the organic layer dried (MgSO4) and evaporated to dryness. The residue was chromatographed using CH2Cl2-EtOAc as eluent to give, after recrystallization from toluene, 2.7 g (35%) of pure white crystals: mp 63-65° C.; 1H NMR δ3.33 (t, 4H, NCH2, J=6 Hz), 3.48 (t, 4H, OCH2, J=6 Hz), 4.43 (bs, 2H, OH), 7.57 (dd, 2H, H2+6, JH2, F3 and H6, F5=8.5 Hz, JH2, F5 and H6, F3=2Hz=22 Hz); 19F NMR δ −116.0 (d, 2F, F3+5, JF3, H2 and F5, 6=7.5 Hz); MS m/z 265 (M+Na+, 10), 243 (M+H+, 100), 211 (M-CH2OH, 85). Anal. (C11H12N2O2F2) C,H,N.

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